Holiday rentals in Osceola

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Top-rated holiday rentals in Osceola

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Guest favourite

Cottage in Stockton

5 out of 5 average rating, 12 reviews

Riverfront Cabin Getaway @ HRF #1 - Sleeps 4

Cabin One is super cozy, featuring a private sleeping loft and a picnic table and fire pit on the waters edge. Learn more about Cabin One: Our cabins, are fully furnished, outfitted with full kitchens, bathrooms, heat and AC. You will have an amazing view of the Sac River from your bed, sofa, patio, and fire pit. Fishing, rafting, swimming & beautiful exploring opportunities abound all within walking distance. Explore our listing more to learn more about Cabin One and Hideaway River Farm!

Guest favourite

Home in Clinton

4.95 out of 5 average rating, 107 reviews

The Orchard House by Katy Trail

Dubbed the Orchard house since being on Orchard street. This newly renovated stand alone home on a quiet dead end road is just what the doctor ordered. Located just 2 miles to the start of the historic Katy Trail makes this a great spot. Also, we are only minutes away from Truman Lake which boasts some of the best crappie and spoonbill fishing around. A dedicated shed with lock is provided at the back of the home for bike storage. A short walk to the historic square with shopping + eateries!

Guest favourite

Treehouse in Stockton

4.95 out of 5 average rating, 117 reviews

Rustic Elegance Treehouse Cabin Stockton Lake, MO

Rustic Elegance tops this Treehouse cabin just a mile from Stockton Lake Dam and 2.5 miles to Stockton Town Center. Enjoy total privacy in this wooded scene looking out over the neighbors cattle as well deer and turkey. Sitting on Bear Creek which is spring fed and a kayak is available to explore the creek for a small fee. Fire pit and Weber grill help round out your evenings pleasures. Grocery store, gas station, restaurants, and shopping are all within 10 minutes. Outside electric included.

Top guest favourite

Home in Deepwater

4.95 out of 5 average rating, 108 reviews

A Cozy Getaway

Minutes away from Harry S. Truman Dam & Reservoir & the upper end of the Lake of the Ozarks. The lake is a popular fishing destination for crappie, largemouth bass, hybrid stripers, catfish, as well as some of the Nation's finest snagging for spoonbill paddlefish. The surrounding area (110,000 acres) provides plentiful & diverse opportunities, including hiking, horseback riding, golfing, biking, bonfires, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

Top guest favourite

Home in Warsaw

4.98 out of 5 average rating, 199 reviews

The Citadel - Close to the Water and Warsaw

The Citadel is a pretty little place, modern with vintage cottage appeal right off Hwy 7 by the mile-long bridge leading into Warsaw. This 2 story, 2 bedroom, 2 full bath home (showers only) offers a well equipped kitchen, dining, living & sitting room w/Roku tv and tv w/dvd player, wifi, room to work, and outdoor seating. Large parking area. Close to swim beaches, the park at Drake Harbor for walking/boating/fishing, flea markets, antique shops, restaurants and the Overlook. No washer/dryer

Guest favourite

Cabin in Wheatland

4.86 out of 5 average rating, 44 reviews

Little Cedar Lodge

Welcome to our charming cabin nestled in a grove of cedar trees. This cozy retreat offers an idyllic escape from the hustle and bustle of everyday life. Wake up to the soothing sounds of nature, and enjoy your morning coffee on the front porch. It is located just minutes from Pomme de Terre Lake, several swimming beaches, boat docks, a state park with fishing access, a walking path, playgrounds, tennis and basketball courts, and volleyball. You will also have walking distance to Dollar General.

Top guest favourite

Cabin in Appleton City

4.97 out of 5 average rating, 76 reviews

Lakeview by Sue Family Cabin

The Family Cabin is one of 5 rustic Cabins of Lakeview by Sue Barn Venue. With its own lake view porch too, it holds a max of 6 guests (note fee for more than 4 guests). When not being rented with a wedding/event, it is offered here for those looking for a serene, country stay. All the kitchen accessories, comfy bedding, and plush towels have been provided. The little lake is steps from your front door where you can enjoy the view and a little fishing too. We hope you enjoy a lovely stay!

Top guest favourite

Cottage in Wheatland

4.97 out of 5 average rating, 395 reviews

Cozy Woodland Cottage

This cozy cottage in the woods (completed in June 2017) is perfect for a couple seeking a romantic getaway, enjoying a honeymoon, or celebrating an anniversary. (The sofa is a full convertible bed, if others plan to share the 400+ sq. ft. space.) Located in the Lake Hill (formerly Shadow Lake) Golf Course neighborhood (course is currently only open seasonally on weekends) about a mile from the NW shores of beautiful Pomme de Terre Lake, and about 6 miles south of Lucas Oil Speedway.

Superhost

Cabin in Pittsburg

4.84 out of 5 average rating, 165 reviews

Wolf Cub Cabin with Private Hot Tub!

The Wolf Cub is one of three cabins located near Pomme de Terre Lake. Reserve this one bedroom cabin for romantic getaway or all three for a group or family gathering. This Cabin has a beautiful fireplace inside and hot tub located in the gazebo off the back deck. Enjoy the hammock and fire pit in the back as well. This cabin is located with in walking distance to the lake where you can put your boat in, swim or fish. Sleeps up to four, full kitchen towels and gas/charcoal grill.

Top guest favourite

Home in Appleton City

4.97 out of 5 average rating, 218 reviews

Tiny Cottage

Escape the big city hustle and bustle for a cozy tiny home with eclectic style in our safe small town of Appleton City. Enjoy the fresh air and open fields. Off street parking. Perfect for a couples get away. There's coffee, toaster, basic kitchen essentials, mini fridge with ice cube trays, lawn chairs for the front porch where you can enjoy your coffee in the morning shade in our quiet little escape. No pets

Guest favourite

Cabin in Osceola

5 out of 5 average rating, 42 reviews

secluded cabin in the Woods - Osceola, MO

This cozy cabin is located 1/2 mile from Weaubleau Creek where there is boat launch access that feeds the Osage River & Truman lake. This is the perfect place for any hunting/fishing trip, or to go do nothing that all! The cabin is secluded, completely unplugged from the outside world. A peaceful retreat for any outdoor or front porch coffee lover. A true gem in any season to recharge free of distractions.

Top guest favourite

Cottage in Wheatland

4.97 out of 5 average rating, 217 reviews

Galmey Grove Cottage

* Wi-Fi Available! *Self Check-In (smart lock) Relax and unplug at our cozy little spot we call Galmey Grove Cottage. Located in Galmey, MO on County Road 273 just off 254 Hwy . We are close to several Pomme de Terre Lake swimming and boat access areas. Another attraction is 8 miles away at Lucas Oil Speedway host to Boat Racing, Off-Road Racing, and Dirt Track Races most weekends April-Oct.

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Other great holiday rentals in Osceola

Cabin in Osceola

4.89 out of 5 average rating, 18 reviews

Peaceful Ozark Getaway

DixieRating, 5 stars1 week ago

I stayed for work but enjoyed the peaceful, Rustic atmosphere and cabin. Caron is very friendly and great to work with! Great place and I can't wait to stay again.

Guest favourite

Cabin in Osceola

4.88 out of 5 average rating, 8 reviews

Rock and Stick Farm

ConnieRating, 5 stars3 weeks ago

Frank made this “getaway” weekend worth it! It was very peaceful and relaxing. He was very responsive when I had my questions. The location was perfect for a quick trip from the city, but close enough to places we wanted to go. I truly enjoyed myself!

Cabin in Collins

4.73 out of 5 average rating, 15 reviews

Iron Horse Dry Cabin 1

ShayleneRating, 5 stars3 weeks ago

your hide out made us feel like home that is close as I could get to our family event you have a great location for every year for us we will be coming back to stay

Guest favourite

Cabin in Hermitage

4.95 out of 5 average rating, 19 reviews

Stony Lane Fishing Cabin

AmandaRating, 5 stars1 week ago

We had a mishap when we checked in, however, Mikayla was super responsive and resolved the issue quickly. She was so apologetic and sweet even while faced with a family emergency out of town. The cabin was cute and cozy. We're talking about going back in the fall. Thanks for being a great host, Mikayla!!

Guest favourite

Cabin in El Dorado Springs

4.96 out of 5 average rating, 26 reviews

El Dorado Springs Cabin: Near Trails & Parks!

EthelRating, 5 stars3 weeks ago

Nice secluded cabin good furniture master bedroom mattress. Is real comfortable well supplied kitchen to do your own meals over all outstandind place yes would return

Top guest favourite

Train in Long Lane

5 out of 5 average rating, 20 reviews

Vintage Luxury Railcar Retreat on 10 acres & Pond

EllieRating, 5 stars2 days ago

We were only able to stay for 1 night but we wish we could have stayed longer! The train was a fun experience for us. We admired the craftsmanship and the smart use of space and The details of products used and decor. I usually can’t sleep well when I’m traveling but the bed was very comfortable and I slept well. Our son caught some fish in the pond he used red worms and they hit on those quickly. If we are ever back in that area we will choose the train again!! The hosts were very nice and helpful!! Great people !!

Guest favourite